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Catalysts
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State-of-the-Art in Asymmetric Organocatalysis
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State-of-the-Art in Asymmetric Organocatalysis

A special issue of Catalysts (ISSN 2073-4344). This special issue belongs to the section "Catalysis in Organic and Polymer Chemistry".

Deadline for manuscript submissions: closed (30 August 2022) | Viewed by 7640

Special Issue Editor

Prof. Dr. Ilya D. Gridnev

E-Mail Website
Guest Editor
N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Science, Leninsky Prospect, 47, 119991 Moscow, Russia
Interests: homogenic catalysis; asymmetric catalysis; mechanism of chirality generation; DFT computations

Special Issue Information

Dear Colleagues,

You are cordially invited to contribute your papers to a Special Issue of Catalysts devoted to a broad and intensively developing area of asymmetric organocatalysis. Submissions of papers covering all aspects in this field are welcome—from purely synthetic results to mechanistic studies and computational investigations.

If enough contributions are assembled in this Special Issue, it can be further published as a book. I hope all specialists in asymmetric organocatalysis will seriously consider submitting a paper for this Special Issue.

Prof. Dr. Ilya D. Gridnev
Guest Editor

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Catalysts is an international peer-reviewed open access monthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • Homogeneous catalysis
  • Asymmetric catalysis
  • Enantioselectivity
  • Chiral compounds

Published Papers (4 papers)

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Research

9 pages, 1438 KiB  
Article
Chiral Bis(8-Quinolyl)Ethane-Derived Diimine: Structure Elucidation and Catalytic Performance in Asymmetric Synthesis of (S)-Warfarin
by Ilya D. Nikitin, Ruslan A. Kovalevsky, Alexander S. Kucherenko, Olga Y. Kuznetsova and Sergei G. Zlotin
Catalysts 2023, 13(1), 136; https://doi.org/10.3390/catal13010136 - 6 Jan 2023
Viewed by 1324
Abstract
C2-symmetric diimine generated in situ from (R,R)-HPEN and 8-formylquinoline was readily transformed to novel chiral diimine pre-III bearing 1(S),2(S)-bis(quinolin-8-yl) ethane and salicylic aldehyde fragments via stereoselective diaza-Cope rearrangement. The structure and absolute configuration of [...] Read more.
C2-symmetric diimine generated in situ from (R,R)-HPEN and 8-formylquinoline was readily transformed to novel chiral diimine pre-III bearing 1(S),2(S)-bis(quinolin-8-yl) ethane and salicylic aldehyde fragments via stereoselective diaza-Cope rearrangement. The structure and absolute configuration of the product was established by the X-ray diffraction study of the corresponding Rh(III) complex. In the presence of pre-III, practically important enantioselective reactions of 4-hydroxycoumarin with α,β-enones afforded anticoagulant (S)-warfarin and its derivatives in aqueous THF in high yield (88–92%) with enantioselectivity 85–93% ee. Full article
(This article belongs to the Special Issue State-of-the-Art in Asymmetric Organocatalysis)
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25 pages, 2112 KiB  
Article
Synthesis and Catalytic Activity of Organocatalysts Based on Enaminone and Benzenediamine Hydrogen Bond Donors
by Luka Ciber, Franc Požgan, Helena Brodnik, Bogdan Štefane, Jurij Svete and Uroš Grošelj
Catalysts 2022, 12(10), 1132; https://doi.org/10.3390/catal12101132 - 28 Sep 2022
Cited by 4 | Viewed by 1649
Abstract
A total of 24 novel organocatalysts based on (S)-quininamine as a chiral tertiary amine and on enaminone or 1,2-benzenediamine as hydrogen bond donors were synthesized. The enaminone-type catalysts were prepared by the transamination of N,N-dimethyl enaminones with ( [...] Read more.
A total of 24 novel organocatalysts based on (S)-quininamine as a chiral tertiary amine and on enaminone or 1,2-benzenediamine as hydrogen bond donors were synthesized. The enaminone-type catalysts were prepared by the transamination of N,N-dimethyl enaminones with (S)-quininamine (9 examples) and the 1,2-benzenediamine-type catalysts were prepared in 3 steps from (S)-quininamine and ortho-fluoronitrobenzene derivatives (15 examples). Their organocatalytic activity was evaluated in the Michael addition of acetylacetone to trans-β-nitrostyrene. Enantioselectivities of up to 72% ee were observed. Full article
(This article belongs to the Special Issue State-of-the-Art in Asymmetric Organocatalysis)
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7 pages, 1219 KiB  
Article
London Disperse Interactions Assist Chiral Induction in the Soai Autoamplifying Reaction Provoked by 1- and 2-Aza[6]helicenes
by Roman V. Zonov and Ilya D. Gridnev
Catalysts 2022, 12(8), 859; https://doi.org/10.3390/catal12080859 - 4 Aug 2022
Cited by 1 | Viewed by 1392
Abstract
In this paper, DFT computations revealed the mechanisms of the asymmetric catalytic reactions of diisopropylzinc with pyrimidylaldehyde catalyzed by 1- and 2-aza[6]helicenes, which make them effective inductors of the autocatalytic chiral amplification Soai reaction. The generation of chirality takes place through the formation [...] Read more.
In this paper, DFT computations revealed the mechanisms of the asymmetric catalytic reactions of diisopropylzinc with pyrimidylaldehyde catalyzed by 1- and 2-aza[6]helicenes, which make them effective inductors of the autocatalytic chiral amplification Soai reaction. The generation of chirality takes place through the formation of adducts of aldehyde and helicenes stabilized via non-covalent disperse interactions strictly defining the orientation of the aldehyde molecule in the corresponding transition state. Full article
(This article belongs to the Special Issue State-of-the-Art in Asymmetric Organocatalysis)
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Graphical abstract

9 pages, 3139 KiB  
Article
Birds of a Feather—Asymmetric Organocatalysis Meets Asymmetric Transition Metal Catalysis
by Ilya D. Gridnev
Catalysts 2022, 12(2), 214; https://doi.org/10.3390/catal12020214 - 11 Feb 2022
Cited by 3 | Viewed by 2475
Abstract
The results of recent studies on the mechanism of stereoinduction in asymmetric hydrogenation catalyzed by transition metal complexes suggest that hydrogen activation by metal atoms and the generation of enantioselectivity by organic ligands proceed independently. Hence, these reactions can be considered as variants [...] Read more.
The results of recent studies on the mechanism of stereoinduction in asymmetric hydrogenation catalyzed by transition metal complexes suggest that hydrogen activation by metal atoms and the generation of enantioselectivity by organic ligands proceed independently. Hence, these reactions can be considered as variants of a cooperative organocatalytic reaction. This conclusion opens a broader view on rational catalyst design, suggesting that the structural ideas from different fields can be exploited reciprocally. Full article
(This article belongs to the Special Issue State-of-the-Art in Asymmetric Organocatalysis)
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